For centuries, Toompea – or the Upper Old Town – was the stronghold of local nobility which consisted mostly of German and Swedish knights’ families. The most influential of them were buried in the Cathedral of Saint Mary the Virgin or the Dome Church. The stone church was established sometime before 1233 and has been repeatedly rebuilt since. The vaulted main body of the present church dates to the 14th century, while its Baroque tower is an addition from the late 1770s. The interior of the medieval building also belongs to the Baroque era, with the high altar (1696) and the pulpit (1686) made by woodcarver Christian Ackermann. The church is filled with elaborate coats of arms from the 17th to the 20th centuries, as well as burial stones from the 13th to the 18th centuries. In 1684, Toompea suffered the most devastating fire in its history. This and several other fires are the reason why Toompea, with its 18th and 19th century representative dwellings of noble families, looks architecturally different and newer compared to the Lower Old Town.

After the bombing by the Soviet Air Force in 1944, the new plan for Tallinn was drawn in 1945 and envisioned a new city centre in the Socialist Realist style. Only fragments of the plan were realized, yet there are numerous buildings from that time that demonstrate how Socialist Realism was interpreted in the Estonian context. By the late 1950s the neoclassical principles of design were cast aside and modernism was introduced in the City Centre, in buildings like the library of the Academy of Sciences (1957–1963), the Communist Party Central Committee building (1964–1968) and the “Intourist” hotel Viru (1964–1972) that was provocatively erected in the vicinity of the Old Town. The tour also visits three major post-war public buildings. The Song Festival Stage (architects Alar Kotli, Henno Sepmann, Uno Tölpus, 1957–1960), that represents the famous Estonian tradition of choral song festivals, was designed to accommodate 30,000 singers. The Flower Pavilion (built 1957–1960) by Valve Pormeister is notable for its sensitive approach to the landscape. The Olympic Yachting Centre was the main location for the sailing regatta of the 1980 Moscow Olympic Games. It is one of the first extensive structures heralding the late-modernist changes in architecture, emphasizing the idea of a building as a complicated system.

The history of the St. Bridget’s Convent in Tallinn – the Pirita Convent – dates back to the 15th century when Tallinn was at its economic peak. The Convent that operated for over 150 years used to be the largest nunnery in Livonia (present-day Estonia and Latvia). Being only partly built upon St. Bridget’s rules, the architecture of the convent church displayed local features. The Convent was destroyed in the 1570s. Since the 1970s, extensive excavation and conservation projects have taken place on the premises of the convent. The massive walls of the church, unearthed parts of claustral buildings on both sides of the church and the graveyard have survived. Today, the ensemble of ruins, a popular concert venue in the summer, is managed by the sisters of the Bridgettine Order.

Nõmme, the former 19th century summerhouse district that was an independent municipality during the interwar years, became a popular area to build modern private villas as well as small apartment houses. During the 1930s, together with a relatively small number of representatives of the wealthy elite, the middle class became the primary group of clients interested in Functionalist architecture. As building in masonry (bricks, limestone, concrete) and steel was still relatively expensive, a large number of Functionalist private dwellings were built of wood.